Controlled crosslinking of latex polymers with polyfunctional amines

1. A polyfunctional amine comprising recurring units derived from the reaction of one bi- or tri-glycidyl moiety and a single, di-, or tri-functional amino monomer(s), or combination of mono/bi, mono/tri, mono/tetra, bi/bi, bi/tri, bi/tetra, tri/tri, tri/tetra, and tetra/tetra functional amino monomers resulting in one or more polyfunctional amines of formulae (I-x) to (I-x-f):

wherein the substituents J, J1, and J2 are the result of a ring-opening reaction during nucleophilic substitution of a bi- or tri-glycidyl moiety,

J is equal to or different than J1 and J2,

J1 is equal to or different than J2,

R1 is selected from the group consisting of: dimethyl amine, diethyl amine, diethanol amine, dipropyl amine, pyrrolidine, piperidine, 1-methyl piperazine, N,N,N-trimethyl-1,2-ethane diamine, N,N,N, triethyl-1,2-ethane diamine, N-methyl-N,N-diethyl-1,2-ethane diamine, N-ethyl-N,N-dimethyl-1,2-ethane diamine, N-methyl-N,N-diethyl-1,3-propane diamine, N-ethyl-N,N-dimethyl-1,3-propane diamine, methyl amine, ethyl amine, 1-propyl amine, ethanol amine, 2-propyl amine, 1-butyl amine, 2-butyl amine, 2-methyl-2-propyl amine, piperazine, N,N-dimethyl-ethyl diamine, N,N-diethyl-ethyl diamine, N,N-dimethyl propyl diamine, N,N-diethyl-propyl diamine, N,N-dimethyl amino propylene amine, N,N-dimethyl ethylene amine, N,N-diethyl amino propylene amine, N,N-diethylamino ethylene amine, amino ethyl-piperazine, N-methyl-1,2-ethane diamine, N-ethyl-1,2-ethane diamine, N-methyl-1,3-propane diamine, N-ethyl-1,3-propane diamine, 1,2-diamine ethane, 1,3-diamino propane, 1,4-diamino butane, cadaverine, cystamine, 1,6-diamino hexane, 1,2-diamine benzene, 1,3-diamino benzene, 1,4-diamino benzene, 1,4-diamino butanol, 4,4-diamino-3-hydroxy butanoic acid, 5-amino-1,3,3-trimethylcyclohexanemethylamine,2,2′-oxybis ethanamine, alanine, and lysine;

R2 and R3 are selected from groups consisting of methyl amine, ethyl amine, 1-propyl amine, ethanol amine, 2-propyl amine, 1-butyl amine, 2-butyl amine, 2-lycmethyl-2-propyl amine, piperazine, N,N-dimethyl-ethyl diamine, N,N-diethyl-ethyl diamine, N,N-dimethyl propyl diamine, N,N-diethyl-propyl diamine, N,N-dimethyl amino propylene amine, N,N-dimethyl ethylene amine, N,N-diethyl amino propylene amine, N,N-diethylamino ethylene amine, amino ethyl-piperazine, N-methyl-1,2-ethane diamine, N-ethyl-1,2-ethane diamine, N-methyl-1,3-propane diamine, N-ethyl-1,3-propane diamine, 1,2-diamine ethane, 1,3-diamino propane, 1,4-diamino butane, cadaverine, cystamine, 1,6-diamino hexane, 1,2-diamine benzene, 1,3-diamino benzene, 1,4-diamino benzene, 1,4-diamino butanol, 4,4-diamino-3-hydroxy butanoic acid, 5-amino-1,3,3-trimethy1cyclohexanemethylamine, 2,2′-oxybis ethanamine, alanine, and lysine,

R1 is equal to or different than R2 and R3,

R2 is equal to or different than R3;

n is a number 1 to 100,

and m is an number equal to or different than n;

wherein the polyfunctional anime of any formulae (I-x) to (I-x-f) is a crosslinking agent bearing

—NH or —NH 2 groups with repeating units, n, and

wherein the —NH or —NH2 group has been reacted with a glycidyl alkenyl compound to introduce an alkene group thereby forming the intermediate structure of formula (I-x-ene);

and wherein introduction of said glycidyl alkenyl compounds to said structure of formulae (I-x) to (I-x-f) occurs only once per repeating unit, n, creating unit of n−1 when treated with additional polyfunctional amines.

2. The polyfunctional amines of claim 1 , wherein said intermediate structure of formula (I-x-ene) when reacted with methacrylic acid and acrylamide, or two other —C═C—functional groups and/or derivatives thereof forms copolymers of formulae (II-x):

Wherein the R1′ is deprotonated R1 except with loss of a proton loss at the NH or —NH 2 site;

wherein R4 is a linking group between a polyamine body of (II-x) and an

alkene functionality and n−1 is a number from four to nineteen;

wherein m is a number from 1 to 100,

o is a number from 1 to 100, and

p is a number from 1 to 100;

wherein repeating substituent R5 results from polymerization of a water soluble monomer having a carbon-carbon double bond, —C═C—; and

wherein the resulting structure exhibits an atomic mass that is greater than or equal to 50,000 Daltons.

3. The polyfunctional amine of claim 2 , wherein when allyl glycidyl ether is present during synthesis, said linking group is —CH 2 CH(OH)CH 2 O—, and

wherein said linking group can also be a connecting glycidyl alkenyl compound that is selected from the group consisting of: allyl glycidyl ether, vinyl glycidyl ether, vinyl cyclohexene oxide, glycidyl methacrylate, glycidyl acrylate, glycidyl acrylamide, and glycidyl methacrylamide.

4. The polyfunctional amine of claim 1 , wherein said polyfunctional amines and intermediate structure of formula (I-x-ene) are crosslinking agents.

5. The polyfunctional amine of claim 1 , wherein said amine is a result of a condensation reaction of a glycidyl group and an amine group, and wherein resulting polyfunctional amine and intermediate structure of formula (I-x-ene) comprise at least three amino groups.

6. The polyfunctional amine of claim 5 , wherein said polyfunctional amine and intermediate structure of formula (I-x-ene) provide an ability to tailor the final molecular weight of said polyfunctional amine.

7. The polyfunctional amine of claim 2 , wherein the repeating substituent R5 results from polymerization of acrylic acid or acrylic acid derivative.

8. The polyfunctional amine of claim 1 , wherein n of said polyfunctional amine and intermediate structure of formula (I-x-ene) is a number from 2 to 100.

9. The polyfunctional amine of claim 1 , wherein n of said polyfunctional amine and intermediate structure of formula (I-x-ene) is a number from 10 to 100.